


So You Want To Date My Mom

by superkim111



Category: Once Upon a Time (TV)
Genre: Alternate Universe - Canon Divergence, F/M, Gen, Humor, Interviews, Matchmaking, Relationship(s), Romance
Language: English
Status: Completed
Published: 2013-08-28
Updated: 2013-11-06
Packaged: 2017-12-24 22:44:58
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 7,557
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/945542
Author URL: https://archiveofourown.org/users/superkim111/pseuds/superkim111
Summary: <blockquote class="userstuff">
              <p>Henry decides to help Emma find happiness by getting her together with her true love. But first he has to interview the candidates.</p>
            </blockquote>





	1. Graham

**Author's Note:**

> I'm sure that by now every Oncer has figured out that you could put Emma in a room with a rock and she'd have chemistry with it. Which is why it's no surprise that she's the subject of so many ships. That's why I decided to make this. To pay tribute to the many couplings of Emma Swan. Now I already have all the chapters written up and posted on other sites but it's going to take me awhile to upload them all here. But they will all be uploaded. So here is the first chapter starring everyone's favorite sheriff and I'll put up the rest of the chapters as soon as I can. Enjoy!

Henry looked over the papers in his hands one last time as he mentally ran through his plan. Emma had been feeling down lately so he'd decided to help her find her true love so that she could be happy again. He'd come up with a list of people to interview and had made information sheets for every single one of them. The hard part would be making sure his mom didn't find out what he was doing. There was no way she'd agree to this. That was why he'd decided to get an early start and had run off right after breakfast. He had a lot of people to see and he had to get the first visit out of the way fast if he didn't want to run into Emma. Once he was satisfied with what he saw he put all but one of the pieces of paper back into the backpack slung over his shoulder. It was time to start Operation Matchmaker. Squaring his shoulders, he took a deep breath and headed into the sheriff's station.

**Candidate Name** : Graham Humbert/The Huntsman

**Occupation** : Sheriff

**How they know Emma:**  Arrested her, made her his deputy, and got his memories back by kissing her

**Relationship Codename:**  Gremma

"So this is for a school project," Graham asked as he and Henry settled in at his desk. He was supposed to be filling out paperwork but he figured it could wait a few minutes.

"Mhm. We're supposed to interview people who work with our parents and that's you," Henry stated as he got out his pen, careful to make sure that Graham couldn't see the top of the paper. He figured it was for the best if his interviewees didn't know what was going on. He wanted honest answers without Emma finding out and this was the best way to get that.

"Alright. What is it you're supposed to ask," the sheriff said with a grin.

"Well first we're supposed to ask some basic questions about whoever we're interviewing. So I need to know your favorite color, favorite animal, and favorite food or drink," he listed off as he poised his pen to start writing. He didn't want to dive in to quickly and it was good to build up a background.

"My favorite color is green, my favorite animal is a wolf, and my favorite food or drink would have to be pixie sticks," Graham answered after a moments' thought.

"A wolf and pixie sticks," Henry repeated with clear amusement. The wolf thing was pretty obvious since he was the Huntsman but weren't pixie sticks supposed to be for kids?

"What? I like them," Graham protested meekly as his grin turned into a sheepish smile.

"Nevermind, let's keep going. What do you think of my mom," he asked as he filled in Graham's answers to the previous questions on his sheet.

"I think Emma's incredible. She's brave and smart and if it wasn't for her I'd never have gotten my heart back from Regina," the sheriff proclaimed, placing his hand over the organ in question. When they'd finally found where his other mom hid all her things Emma had immediately brought Graham down there so they could look for his heart. It had taken them awhile but they'd managed to find it and the sheriff had never been happier. Literally.

"And what do you two do together now that the curse is broken," Henry continued.

"Well we work together, obviously. We answer calls and go out on patrol with your grandfather. We've hung out at Granny's as well. I figure I owe her a couple free meals," Graham replied with a chuckle. He owed her more than a couple really. She'd saved the entire town after all.

"Last question. What's one thing you regret saying or doing to my mom," he said, looking up expectantly. He'd never heard of Graham doing anything that upset Emma besides arresting her those few times but he had to have done something he wished he could take back.

"That's a strange question for a school report," the sheriff stated, clearly a bit suspicious.

"I think it has something to do with how well you work with each other," Henry lied. If Graham figured out he wasn't being honest then he'd tell Emma and the entire operation would be ruined.

"Alright well in hindsight it probably wasn't the best idea to throw a dart at her head," Graham confessed with clear embarrassment.

"You did what?!"

"I know, I shouldn't have done it but I wasn't exactly myself at the time. And I didn't hit her or anything," the sheriff quickly explained. He did a lot of things that night he wouldn't have done if he was himself. Though not all of them were necessarily bad. He didn't regret kissing Emma at all. That was what let him get his memories back and help her. True their relationship ship hadn't gotten any further but they'd both agreed that with all that was going on it was for the best. Back then it had been an angry Regina and now it was a magical town full of confused people and an angry Regina.

"And was this before or after you kissed her?"

"Before."

Henry quickly added that to his sheet before giving it a quick once over. That was it, he'd filled in all the blanks. And while some of the answers hadn't been what he was expecting it was still good progress.

"That's all I needed. Thanks for the help Graham," he chirped as he gathered up his backpack and put the paper inside.

"No problem. You know your mother should be here soon, you can stick around and talk to her if you want. I think she's bringing doughnuts," Graham offered as he started to stand.

"No thanks, I'm gonna get going. See you later," he said before getting up and hurrying outside and down the street.

Next stop, Gepetto's repair store.


	2. August

**Summary for the Chapter:**

> Henry decides to help Emma find happiness by getting her together with her true love. But first he has to interview the candidates.

**Notes for the Chapter:**

> Well here we are, the second chapter of So You Want To Date My Mom. In this installment of the series we get to see our intrepid young matchmaker Henry interview none other than August Booth. Because if I can have Graham be alive, I can have August be an adult.

Henry heard the chime of a bell as he walked into Gepetto's shop. Now that August was human again and had stopped avoiding everyone he'd started working with his dad at his store.

"Ah, good morning Henry. What can I do for you today," Gepetto asked as he looked up from the clock he was working on at the counter.

"Actually I was wondering if I could talk to August," he answered hopefully as he took a seat on an empty stool.

"Of course. He's in back, I'll go get him," the elderly toy-maker replied, putting down the tools in his hand and going through the door that lead to the back of the shop. While he waited Henry rifled through his backpack for August's information sheet.

"I need to go get some things from the hardware store. Could you look after the shop for me," he heard Gepetto say as the man returned with his son in tow.

"Sure thing Papa. Hey Henry! What's up," August asked, taking his father's place behind the counter as the man himself left to run his errand.

Henry smiled as he pulled out the piece of paper he was looking for.

"I was hoping I could ask you some questions for a school project."

**Candidate Name** : August W. Booth/Pinocchio

**Occupation** : Writer and Repairman

**How they know Emma:**  Traveled with her from Fairy Tale Land and tried to get her to believe in the curse

**Relationship Codename:**  Wooden Swan

"Alright, first questions. What's your favorite color, favorite animal, and favorite food or drink," Henry asked once August had agreed to the interview. He'd had a bit of trouble coming up with a reason why he had to talk to him specifically so he'd tried to be as vague as possible. He wasn't sure August had completely bought it but he was still going along with it and that was all that mattered.

"I like the color red, my favorite animal is a cat, and my favorite drink is coffee," August replied as he tinkered with the clock that his father had left on the counter.

"Why coffee," Henry inquired, confused as to why someone would choose that as their favorite drink. He'd tried to get some himself before but that was just so he could be alert and ready for Operation Cobra.

"It's a writer's best friend," August explained with a shrug as though that explained everything. Of course he hadn't done much writing since he'd started turning back to wood last year. He'd been too preoccupied. Maybe he'd start up again once he was more settled in.

"Okay, next I need to know what you think of my mom," Henry said even though he wasn't really satisfied with his explanation. But it wasn't like this was the first time the former puppet had given vague answers to somebody's questions. He just hoped he wouldn't do that with this one.

"Your mom is...incredible. I wouldn't be able to do half of the things she's done," August answered with a slight shake of his head. And he knew that for a fact too. All these years whenever something gone wrong he'd just ran away. Emma had never run. She'd stayed and she'd fought. Even if it didn't seem like she could win she had fought. He would consider himself lucky to have even a tenth of her inner strength.

"And what do you two do together now that the curse is broken," Henry continued while writing down the answers he had received on the sheet. It sounded like there was more to that last one but he didn't want to risk scaring him off by asking about it.

"We've met up at Granny's a few times to talk," August stated before returning his attention to the clock. Their first conversation after his near-death experience had mostly consisted of her yelling at him about Neal with him trying to stammer out excuses. It was a bad habit of his that he hadn't quite kicked yet. After that she had grilled him for information about who he had tried to warn her about. Unfortunately when the Blue Fairy had brought him back his short term memory had been affected. He remembered talking to Snow White and had a vague sense of foreboding but that was it. He had promised that he'd call her if the memories came back though and in the meanwhile he was working on redeeming himself to her. It wasn't going to be easy, not with all the crap he'd pulled, but it would be worth it.

"Final question. What's one thing you regret saying or doing to my mom," Henry asked, secretly very curious about what he'd choose. He knew that August had made some pretty big mistakes when it came to his mom. Some of them he'd been told about, some of them he'd 'accidentally' overheard. But he also knew that August had changed. The fact that he was able to be brought back was proof of that.

"There's a lot of things I regret," August said softly as his hands stilled.

"So choose one," Henry prompted.

"I regret not being there for her," August finally replied, looking up at Henry with a sad smile.

"But you're here for her now, right? You can still help her," Henry stated with a grin.

"I'm going to try," August answered before awkwardly clearing his throat and adding, "Anyway if that's the last question I should probably get back to work. Mr. Gold wants his clock repaired and we all know how he gets when people let him down."

"Right. I've got to get going anyway. Thanks for answering my questions," Henry beamed as he put the paper back into his backpack and slid off the stool.

"Happy to help. And tell your mom I said hi," August called as Henry ran out of the shop.

He needed to keep moving and it was going to take awhile to get to Grace's house.


	3. Jefferson

**Summary for the Chapter:**

> Henry decides to help Emma find happiness by getting her together with her true love. But first he has to interview the candidates.

**Notes for the Chapter:**

> With a spin of my hat, I transport you to a magical land where you find the third chapter of this story. But why use a hat? Because this chapter is about Jefferson! Speaking of which I probably should give him his hat back. Otherwise he really will be the Mad Hatter. See ya!

Henry rocked back on his heels and listened to the sound of the doorbell reverberating through Jefferson's house. It had taken him awhile to get to it since it was so far away but Operation Matchmaker wouldn't be complete unless he interviewed every candidate.

"Henry. What brings you here," Jefferson asked after opening the door. While he waited for an answer he quickly scanned the rest of his porch and driveway for any of the kid's relatives. Interestingly enough it seemed that he'd come alone. That was quite a walk. And not very safe either. He'd have to give Emma a call about that.

"Sorry to bother you but I was wondering if I could ask you some questions about my mom," Henry asked with a hopeful smile. He knew that he couldn't lie to Jefferson and say it was for school. All he'd have to do is ask Grace about it and his cover would be blown. So he'd have to use a different excuse.

"Well I suppose it would be a shame if you came all this way for nothing," Jefferson mused before half shrugging and opening the door wide.

"Come on in."

**Candidate Name** : Jefferson/Mad Hatter

**Occupation** : Hat Maker

**How they know Emma:**  Kidnapped her and got his butt kicked by Grandma

**Relationship Codename:** Mad Swan

"So let me get this straight. You're making a database of all the people in Storybrooke and how they know your mom and you want me to be in it," Jefferson stated as he gently placed the cup of tea he'd been drinking on the table in-between them.

"Mhm. Emma's been having a bit of a hard time adjusting and I wanted to help her out," Henry replied with a nod while tapping the sheet of paper laid out in front of him. Technically he was trying to help her by making profiles about people. It was just for a different reason and less people were involved.

"I suppose that makes sense. Ask away," Jefferson proclaimed, throwing out his arm as he leaned back in his chair.

"Great! Okay, first off I want to make a basic profile. So I need your favorite color, your favorite animal, and your favorite food or drink," Henry said as he poised his pen to start writing.

"I like the color purple, my favorite animal is a rabbit, and in case you hadn't figured it out my favorite drink is tea," Jefferson answered while gesturing at the cup in front of him to illustrate his point. His fondness for the drink was admittedly quite obvious but there was a reason it featured so heavily in his story.

"Aren't rabbits Grace's favorite animal," Henry mused, his hand pausing in its writing. He remembered her saying something like that once. And he'd seen her wearing clothes with rabbits on them before.

"So they are," Jefferson confirmed with a smile. She'd always loved rabbits, even as a baby. That was why he'd wanted to buy her that stuffed rabbit in the market so badly. And why he'd made her one himself when he couldn't get it. There were benefits to being good with fabric.

"Alright well let's get to the important stuff. What do you think of my mom," Henry asked after quickly filling in the hatter's answers.

"What do I think of your mom. I think she's...magical," Jefferson said as his smile turned into a smirk.

"Seriously," Henry deadpanned, clearly unamused.

"Sorry, I couldn't help myself," Jefferson replied with a laugh. Once he was done though he did think it over. What was his opinion of Emma Swan, savior of Storybrooke?

"I believe that your mother is a strong woman who'll go to great lengths to take care of her family. And I can respect that. However sometimes she has...difficulties in believing. You might want to work on that with her," he answered before grabbing his cup and taking another sip of his tea. Belief was so important after all. You were nothing if you didn't have something to believe in. Whether it was family or magic or some grand cause. But Emma had trouble with that. Sure sometimes she was able to wholly believe in herself but he'd even seen her have trouble with that sometimes. And that was a dangerous thing. He had faith that she could learn though now that she had more people to help her.

"And what do you two do together now that the curse is broken," Henry continued after making a mental note to bring that up with his mom. The hatter had a point after all. It had taken him forever to get her to believe in the curse.

"We've talked. Your grandfather acting as chaperone of course. He still doesn't quite trust me. But I've heard that you put in a good word for me. Thank you," Jefferson stated with a nod of his head. Henry was a good kid and Grace liked him. He just hoped that Charming would listen. After all there were only so many times a man could apologize before he started to sound like a broken record. Even Emma seemed to have warmed up to him and he'd done more to her than he'd ever done to the Prince.

"No problem. What you did was wrong but you just wanted your daughter back and honestly you got hurt more than anyone else. Besides you've helped us out a lot since then and Belle said that you were the one who freed her from the hospital," Henry pointed out with a bright smile.

"She told you that," Jefferson asked with slight surprise.

"Not exactly. I may have been eavesdropping," Henry confessed sheepishly. He'd found a spot upstairs that let him hear everything Emma and his grandparents talked about in the kitchen. It was a great way to get information on things.

"Don't worry, your secret's safe with me," Jefferson replied with a chuckle. God knows he'd done his share of spying on people. That was what his telescope was for.

"Thanks. Anyway I've got one last question. What's one thing you regret saying or doing to my mom," Henry said though he was pretty sure he already knew the answer to that one. Still it would be nice to have it in Jefferson's own words.

"I regret the way I treated her when we first met. If I'd taken a more gentle approach things probably would have gone a lot differently," Jefferson answered with a sigh. He wouldn't have gotten the crap kicked out of him, the Charmings wouldn't have reason to mistrust him, and who knows they might have even helped him get his Grace back without him having to deal with Regina. Though technically if he hadn't have gotten the Queen her apple the series of events that lead to the curse breaking wouldn't have occurred. But he thought it would be best if he kept that to himself. At least for now.

"That's all I need. Thanks for letting me interview you," Henry proclaimed, looking over the piece of paper one more time before putting it back in his backpack.

"Not so fast. There's no way I'm going to let you walk back to town all by yourself. So are we going to walk or do you want to take my car," Jefferson asked as he rose to his feet. This way Henry wouldn't run into any trouble and he could pick up some groceries. He hoped Henry chose the car though. He'd given him a choice because he didn't want to make the kid uncomfortable but it would be a lot easier on him to just drive.

"The car's okay. Can you drop me off at my house," Henry asked while slinging his backpack over his shoulder.

"Sure thing," Jefferson called as he grabbed his car keys off the kitchen counter and opened the door to the garage.

Henry quickly ran after him and when Jefferson unlocked his car he slid into the passenger seat.

He had a lunch date with his dad to get to.


	4. Neal

**Summary for the Chapter:**

> Henry decides to help Emma find happiness by getting her together with her true love. But first he has to interview the candidates.

**Notes for the Chapter:**

> What time is it? Once Upon A Time! Sorry, couldn't help myself. Anyway I am proud to present to you the fourth chapter of So You Want To Date My Mom starring none other than Henry's dad, Neal aka Baelfire. After this there will be one more interview and then the final chapter will be upon us. But that's still not for awhile yet so for now let's just enjoy this update.

"Thanks again for the ride," Henry yelled with a wave as Jefferson drove away down the street. Once the car was out of sight he quickly ran into the building and headed to the loft. When he got inside he was pleased to see his dad sitting at the counter with a bunch of food laid out for them.

"Hey Henry. I got everything set up for us," Neal proclaimed with a dramatic sweep of his arms. It seemed like he was gesturing like that more often. Hopefully it wasn't his father rubbing off on him. Don't get him wrong, his dad was trying to be a better parent but he still wasn't what you'd call a role model.

"Great! Hey dad, can I ask you something," Henry said as he took off his backpack and hopped up on a chair next to Neal. He was careful to put the backpack right at his feet though. If his plan worked he wanted to be able to get out his dad's interview sheet right away.

"Of course," Neal stated with a shrug as he pushed a plate of food towards Henry. He knew it had all of his favorites on it because he'd been trying to find out as much as he could about his son since they'd met.

"You see, I have this school project and we're supposed to interview one of our parents. I was wondering if maybe I could interview you," Henry asked after taking a bite out of the sandwich on his plate. He knew that getting Neal to agree was important but he hadn't eaten anything since he'd left the house that morning and he was starving.

"I don't know kid. You sure you don't want to interview to your mom instead," Neal replied nervously. There was a lot of stuff about his past that he didn't want Henry to know about. At least not yet.

"I thought about it but I've spent the last year learning about Emma. I want to learn about you," Henry said earnestly. It was true. He did want to know more about his dad. But he was also guilt-tripping him and he felt kinda bad about that. He was sure that this would help Emma though and who knows maybe it would help Neal too.

Neal ran his fingers through his hair with a sigh. The kid had a point. Henry'd probably spent his whole life wondering about him and now that he was here he wasn't telling him anything about himself. How were they supposed to connect, really connect, if he didn't open up? He was just so afraid of saying the wrong thing or letting something slip. But he couldn't afford to be like that. That was cowardly and there was no way he was going to risk ruining his chance with his son just because he wasn't brave enough to take a chance. Making up for all the years they'd lost wouldn't be easy but maybe this would be a good start.

"Sure. Ask away."

**Candidate Name** : Neal Cassidy/Baelfire

**Occupation** : Dad

**How they know Emma:**  Met when they were younger and had me

**Relationship Codename:**  Swanthief? Swanfire?

"So first I need to know your favorite color, your favorite animal, and your favorite food or drink," Henry stated happily after getting a pen and his dad's paper out of the backpack beneath his feet. He was so glad that Neal had said yes even if he had needed a little push.

"My favorite color is yellow, I love dogs, and my favorite food is bread," Neal answered after taking a drink from his glass.

"Why's that," Henry pressed even as he recorded his father's answers. He didn't need it for the profile but he really did want to learn more about him. He hadn't been lying about that.

"Well yellow's a nice color, I played with some great dogs when I was a kid, and bread's just delicious," Neal explained before taking a bite of his own sandwich. Yellow hadn't always been his favorite color though. Hell when he was a kid he rarely even saw it. But when he got older it started to grow on him. The fact that he'd started to associate it with Emma probably had something to do with that. It was the color of her hair in the sun and the car that had brought them together. The car that she still drove around. He was glad that she'd at least gotten that after he split town.

"I see. Okay, next question. What do you think of mom," Henry asked, taking a sip from his glass of milk before returning his attention to the paper in front of him.

"I thought this interview was supposed to be about me," Neal said with equal parts confusion and suspicion. This wouldn't be the first time Henry tried to pull something on him. Of course last time he'd actually managed to pull it off. The kid was crafty, he'd give him that. He just wished he wouldn't use it against them.

"It is. But we're supposed to ask about our other parent too," Henry reassured him. If his dad figured out he wasn't telling the truth he'd be in trouble.

"Mhm. Alright I think your mom is amazing. She got dealt a bad hand in life but she never let it beat her. She just kept going and if something got in her way she found a way to deal with it," Neal replied though he still wasn't quite convinced. He was telling the truth though. Emma was a survivor. Once they got together and she started to trust him she'd told him about all the crap that she'd had to go through growing up. A lesser person would have broken. But Emma, Emma just got stronger. She adapted. She learned. She did whatever it took to make it another day. And yeah there were consequences to that but as long as you were alive you could deal with those.

"And what do you two do together now that the curse is broken," Henry questioned while picking up his sandwich with his free hand and finishing it off. His dad really was good at making them. But they were probably pretty hard to mess up.

"We both spend time with you. And of course we've gotten together to talk about things," Neal answered with a half shrug.

"Like what kind of things," Henry asked curiously. He knew that they'd been meeting up at Granny's sometimes but neither of them would tell him what they talked about.

"Just, you know, things. About how we're gonna work all this out," Neal said, finishing off his food in an attempt to keep Henry from asking him to go into detail. The meetings between he and Emma were a mixed bag. On one hand they were both determined to make this work and that meant talking to each other. But there were still some touchy subjects between them. Like the fact he'd let a puppet convince him to abandon her. He hadn't forgiven himself for that anymore than she had. They were trying though.

"Uh-huh. Alright, last question. What's one thing you regret saying or doing to mom," Henry stated though he made a mental note to try and find out more about his parents' meetings. Maybe he could get Ruby to help him.

"Umm, I wish that things hadn't ended between us the way they did," Neal replied after taking a moment to figure out how to phrase it. He wished a lot of things hadn't gone the way they did. He wished he could have stayed with Emma and moved to Tallahassee like they'd planned. He wished that they could have raised Henry together. And maybe the Curse would have found a way to draw her in but at least they would have been together.

"If it makes you feel better Emma really seems to be warming up to you," Henry comforted him with a smile. He wouldn't have put his dad on the list if she wasn't.

"Thanks Henry," Neal said with a smile of his own.

"You're welcome. Anyway that's all I needed. Thanks for letting me interview you," Henry replied before focusing on eating the rest of the food on his plate.

"Any time," Neal stated before turning his attention to his own plate.

The two of them spent the next half an hour or so talking about whatever came into their heads. Anything from sports to school to New York was a viable topic. And while they didn't talk any more about Neal and Emma's past relationship other than a passing remark they both did learn more about the other.

"Say, maybe we can do this again sometime. Have lunch just the two of us," Neal suggested as their lunch drew to a close. Maybe they could even make a thing out of it or something.

"That sounds like fun. Well I gotta get going. I'm meeting up with some friends at the park," Henry said cheerfully as he gathered up all his things. He'd really enjoyed hanging out with his dad like this even if it wasn't as exciting as their sword fighting lessons.

"I've got some stuff to do too. Have fun, alright," Neal replied as he gathered up their dirty dishes and took them over to the sink. He doubted that the Charmings would appreciate the two of them leaving a mess behind for them to clean up.

"I will. See you later," Henry proclaimed before slinging his backpack over his shoulder and heading out the door.

It was time to head over to the docks and track down a pirate ship.


	5. Killian

**Summary for the Chapter:**

> Henry decides to help Emma find happiness by getting her together with her true love. But first he has to interview the candidates.

**Notes for the Chapter:**

> Here we are, the second to last chapter of So You Want To Date My Mom. In this chapter, as the title suggests, Henry interviews a certain swash-buckling rogue. So buckle your seat belt and get ready for some innuendo because it seems like Hook just can't help himself. Not even when there's a child with him. Poor Henry.

Henry's hair fluttered in the breeze as he walked down the docks looking for the Jolly Roger. It wasn't where he and his family had docked it when they'd gotten back from New York but that didn't really surprise him. If someone stole his ship he'd move it when he got it back too. Luckily for him though it didn't take very long to find the spot it had been moved to.

"Hello? Captain Hook," Henry called as he scanned what he could see of the deck from his spot on the docks. He hadn't thought of it before but what if he wasn't there? He couldn't just go around town looking for him. Luckily his fears were put to rest when the pirate in question peered over the side of the ship.

"Ahoy there! You're Swan and Baelfire's boy, Henry, correct," Killian called in response as he looked the boy over. He could definitely see the familial resemblance. But what he couldn't see were the lad's parents. And since he doubted that either of them would let the boy visit him unaccompanied that meant he was here in secret. Interesting.

"That's me! Permission to come aboard," Henry asked hopefully.

"Permission granted," Killian answered with a nod. He was curious as to what had brought the boy here. And what lad didn't want to spend time on a pirate ship?

Henry smiled before adjusting his backpack and heading over to the gangplank. By the time he got up on deck Hook was already waiting for him with open arms and a large grin.

"Welcome aboard the Jolly Roger my boy."

**Candidate Name** : Killian Jones/Captain Hook

**Occupation** : Pirate

**How they know Emma:**  Fought with her and against her in the Enchanted Forest

**Relationship Codename:**  Captain Swan

"So tell me, what brings you to my ship on this fine day," Killian asked, gesturing around him with his hand before walking towards the stern.

"Actually I was wondering if you could help me with something. You see, I'm supposed to write a report for school about how relationships develop and I thought that maybe I could write mine about you and my mom. But in order to do that I need to ask you a few questions," Henry explained while following the pirate up the stairs towards the wheel.

"I see. And is that the only reason you sought me out," Killian inquired as he stopped to lean against the side of the ship.

"That and I kinda wanted to see your ship again," Henry admitted with a shrug and a smile. He might be on a mission but the Jolly Roger was the most famous pirate ship in the world.

"An understandable desire. Very well. I'd hate to stand in the way of your education. Ask me anything you wish," Killian proclaimed with a chuckle. So he'd been right though he suspected the lad was, in fact, holding out on him. But he couldn't see any harm in answering the boy's questions.

"Alright, first we're supposed to collect basic information about the person we're interviewing. So I need to know your favorite color, your favorite animal, and your favorite food or drink," Henry said while looking around for a surface to write on. There was probably enough room on top of the wall Hook was leaning on but he didn't want to risk losing the paper. So he ended up using the wood block the ship's wheel was attached to as a table.

"I'm quite fond of the color black, I've recently gained a certain appreciation for swans, and rum is my beverage of choice," Killian replied as he straightened up and moved so he was directly in front of the ship's wheel and directly in Henry's line of sight. He found that asking people questions worked better when both parties could see the other.

"Kinda like Jack Sparrow," Henry mused before carefully jotting down the pirate's answers.

"Who," Killian asked with clear confusion. He had learned much of this realm since he had arrived with Cora but the name was unfamiliar to him.

"Never mind. So what do you think of my mom," Henry continued with a grin.

"Your mother is a very unique individual. Not many can say they've bested me yet she seems to have a certain knack for it. It's as intriguing as it is infuriating," Killian stated with a fond smile. He'd told her as much himself when they first met in the Enchanted forest. Even then she'd been ruining his plans. It was what piqued his interest in her in the first place. Their joint effort to climb the beanstalk and subdue the giant had only furthered those feelings. However her leaving him behind had left a rather sour taste in his mouth. He liked to tell himself it was just because he preferred to be the one doing the double-crossing but he knew that wasn't true. The truth was that he'd grown fond of her. And she'd left him shackled in the castle of a giant for his troubles. Even if he could understand the reason behind her actions it still stung.

"And what do you two do together now that you're not a bad guy," Henry asked once he'd finished writing what Hook had said.

"We've had words. Your mother seems to think I'll get into all sorts of mischief if she's not there to police me. Not that I mind her company," Killian teased as his smile turned into a smirk. Even after coming to an admittedly uneasy peace with his crocodile Emma still didn't quite trust him. But he had faith that she'd come around eventually. She already enjoyed their little run-ins whether she admitted it or not. It was as plain as the nose on her face. Then again he always had been able to read her like an open book. The only problem was that she was getting better and better at reading him as well. That could cause him some trouble further along the line. However until that time came he was more than happy to continue their verbal spars as they were.

"Alright now there's just one more question I have to ask. What's one thing you regret saying or doing to my mom," Henry said after rolling his eyes at Hook's flirting. He made sure to write a note about that on the information sheet.

"I regret not giving her a second chance. If I'd been more willing to forgive we could have avoided quite a bit of unpleasantness," Killian replied, his expression turning a twinge sorrowful. He had no doubt that things would have gone quite differently if he hadn't re-joined with Cora. Maybe it would have even inspired some of the trust that his Swan seemed so loathe to give. But if they had brought him with them what would have happened when he went after his crocodile? He doubted they'd have let him kill him. The only question then was how he would respond to that. Give up on his vengeance or cut ties with them and go at it alone. He had a feeling he knew which one he would have chosen. So perhaps things happening the way they did was for the best.

"Well that's all I needed to know. And I should probably get going. I don't think my parents would like me hanging around here. But thank you for helping me," Henry stated, carefully reading over Hook's answers one more time before putting the sheet of paper safely inside his backpack.

"You're most welcome. And don't worry, I won't breathe a word of your visit to anyone. However I do expect to read a finished copy of that report. Just to make sure you got all the details right," Hook said while he and the boy both headed back down towards the gangplank.

"Sure thing. See you later," Henry replied with a wave before getting off the ship and heading back towards town. He didn't know how he was going to come up with a paper to show Hook but he was sure he could think of something.

For now though it was time to head back home.


	6. Emma

**Summary for the Chapter:**

> Henry decides to help Emma find happiness by getting her together with her true love. But first he has to interview the candidates.

**Notes for the Chapter:**

> *sings* So long! Farewell! For this is the end! It's been, so fun, to have you along my friends! This is the final chapter here but do not worry, never fear, for we still have the show that we all hold dear! But for this, at least, it's the ennnnnnd! *bows to applause*
> 
> Sorry about that guys but I've always loved a big finishing number. Alas, as my impromptu ditty said, this is the final chapter, and therefore the end, of So You Want To Date My Mom. I am so happy that so many people have enjoyed this story and read along, rooting for their favorite ship all the way. And so it is both a pleasure and an honor to present to you chapter six of So You Want To Date My Mom, starring none other than Henry Mills and Emma Swan herself!

Henry was quite pleased with himself as he walked back home. He had managed to interview every candidate without any of them catching on to what he was really doing. Now he just had to review the files and figure out which one of them was his mom's true love. He knew it might take awhile, this was an important decision, but he was sure he could pull it off.

A brief honk of a car horn startled him out of his thoughts. Turning slightly, he watched as Emma drove up to him and pulled over onto the side of the street. "Hey kid. Hop in," she with a smile and a jerk of her head after rolling down the passenger side window. Henry smiled in return before opening the door and piling inside. Getting a ride with his mom would be a lot quicker than walking.

"So how did your day go," Emma asked, briefly glancing at him as she drove away in the direction of the loft.

"It went good," Henry stated with a nod. The less Emma knew about his day the better. He didn't want to say something only to say something else later and end up giving the whole thing away.

"Just good? Nothing else you want to add to that," Emma pressed with a wry grin. Usually when she asked that question she got a full day's report. Not that she minded. It was nice knowing what Henry got up to while she was at work.

"Nope. What about you," Henry asked brightly in order to draw attention away from himself.

"You know, it's funny you should ask because I spent all day hearing about you," Emma said with the distinct tone of someone who knew that they knew something they weren't supposed to know.

"W-What do you mean," Henry replied while trying his best not to look nervous. There was no way she could know what he'd been doing. Could she?

"Well when I got to the sheriff station this morning Graham mentioned that you'd asked him some questions for a project and had just left. When I was doing my rounds I stopped to talk to Geppetto who mentioned that you were in his shop talking to August. I was getting off my lunch break when Jefferson called and told me you'd walked to his house by yourself, asked him some questions, and then had him drop you off back at home. So I called up your dad and he said you'd asked him questions for a school project too. And just now I caught you walking back home from the docks. So spill. What are you up to," Emma asked with a look that clearly said that the jig was up. Henry had no reason to go and visit all those people, especially in secret. And he was definitely trying to keep this a secret from her. But he should know by now that she always found out sooner or later.

"I'm just working on a school project. Like everyone said," Henry answered eagerly. Maybe a bit too eagerly. Oh man, he was in trouble.

"I see. So you wouldn't mind if I talked to Mary Margaret about this school project," Emma said, placing special emphasis on the last two words to let him know that she wasn't buying it for a second. Henry was definitely up to something and she was going to find out what that was.

Henry wracked his brain trying to think of a way out of this. But no matter how hard he tried he couldn't come up with anything. There was just no way to explain why he'd visited all of them without giving everything away. "Okay," he admitted reluctantly with a sigh, "I was working on my latest mission."

"And what mission is that? Operation Tarantula," Emma joked with a grin.

"No, Operation Matchmaker," Henry replied.

"What," Emma stated with obvious confusion.

"Well you've just seemed so sad lately and I thought that if I helped you find your true love it'd make you happy again. So I put together some files on all the guys I thought you could get together with," Henry explained, suddenly feeling very stupid.

"Oh Henry," Emma breathed out as her face fell. It was true she hadn't been feeling her best lately, a lot had happened after all, but she had no idea that it was effecting him. If she'd known that she would have...done something. She didn't know exactly what but all the stuff that was going on was her problem, not his. And she'd been teasing him about it too! Man did she feel like a crappy parent.

Henry shuffled his feet, suddenly very interested in the floor of his mom's car. What had he been thinking? That he could just choose someone for his mom to date and everything would be fine? What a dumb idea. But he found himself looking up at his mom when she removed one of her hands from the steering wheel and placed it on his own.

"Look, I appreciate you trying to help me out but I'm not looking for true love. Right now my main concern is looking after you. You're the guy in my life and you make me happy," Emma said with a soft smile. She wanted to be sure that Henry knew just how much he meant to her. When she felt like it was her against a world ruled by Regina Henry had been the one to give her hope. Henry was the one who inspired her to keep on fighting. Honestly now that she had Henry she didn't know what she'd do without him.

"Really," Henry asked with a small, hopeful smile.

"Really. So if you ever get worried about me all you got to do is come and talk to me. No more interviewing every guy in Storybrooke," Emma joked with a grin. Though she had to admit she did admire his dedication. He'd traveled around the entire town and she'd gotten lost enough times to know for a fact that Storybrooke was bigger than it looked.

"Not every guy. Just the ones you have chemistry with," Henry corrected, his smile now a full on grin. His mom always did know how to cheer him up when he was feeling bad. Maybe it was a second superpower or something.

"Henry," Emma warned though it was obvious that she was just joking.

"Alright, alright, no more interviews," Henry conceded with a laugh.

"Thank you. Now how about you and I go get some ice cream at Granny's and you can show me those files you made," Emma offered, giving Henry's hand one last pat before returning her own to the wheel. Ice cream made everything better, right? She sure could go for some.

"I thought you said you weren't interested in finding your true love," Henry questioned with a little bit of a smirk.

"I'm not. But that doesn't mean I don't want to know what everyone said," Emma replied, a look on her face that some might call downright deviant. After all, Henry didn't just get his mischievous streak from his dad.

"Then Granny's it is," Henry beamed with a nod.

Maybe Operation Matchmaker wasn't such a bust after all.

**Notes for the Chapter:**

> Annnnnnd that's a wrap! I would like to thank all of you who have read this story, left a comment, pushed that nifty little kudos button, or did anything else to show your support. It means a lot to know that so many people have enjoyed this little exploration of Emma's love life. Now, for the final time, I'd like to encourage you to leave at least one more little comment telling me what you thought about this chapter or the story in general. Maybe share your favorite line, moment, or chapter. I, as always, love to hear from you. Good night everyone. Please do drive home safely.


End file.
